Electro-polarizable compound and capacitor

Patent metadata

Field	Value
Publication number	US-10707019-B2
Application number	US-201815982482-A
Country	US
Kind code	B2
Filing date	May 17, 2018
Priority date	Apr 4, 2016
Publication date	Jul 7, 2020
Grant date	Jul 7, 2020

Abstract

An electro-polarizable compound has the following general formula:

where Core1 is an aromatic polycyclic conjugated molecule having two-dimensional flat form and self-assembling by pi-pi stacking in a column-like supramolecule, which is tetrapirolic macro-cyclic fragment, R1 is an dopant group connected to Core1, m is number of R1 which is equal to 1, 2, 3 or 4, R2 is a substituent comprising one or more ionic groups, p is number of R2 which is equal to 0, 1, 2, 3 or 4. The fragment marked NLE containing the Core1 with at least one R1 has a nonlinear effect of polarization. Core2 is an electro-conductive oligomer self-assembling by pi-pi stacking in a column-like supramolecule, n is number of Core2 which is equal to 2, or 4, R3 is a substituent comprising one or more ionic groups, s is number of R3 which is equal to 0, 1, 2, 3 or 4. R4 is a non-polar resistive substituent, k is a number of R4 which is equal to 0, 1, 2, 3, 4, 5, 6, 7 or 8.

First claim

What is claimed is:

1. An electro-polarizable compound having the following general formula (I):

where Core1 is an aromatic polycyclic conjugated molecule having two-dimensional flat form and self-assembling by pi-pi stacking in a column-like supramolecule comprising one or more rylene fragments selected from structures 1 to 12:

or a tetrapirolic macro-cyclic fragment that has a general structural formula form the group comprising structures 13 to 19, where M denotes an atom of metal or two protons (2H):

R1 is an dopant group connected to the aromatic polycyclic conjugated molecule (Core1) selected from nucleophilic groups (donors): —NO 2 , —NH 3 + and —NR 3 + , counterion Cl − or Br − , —CHO, —CRO, —SO 3 H, —SO 3 R, SO 2 NH 2 , —COOH, —COOR, —COCl, —CONH 2 , —CF 3 , —CCl 3 , —CN, wherein R is radical selected from the list consisting of alkyl, allyl, benzyl groups, phenyl, substituted phenyl and other aryl groups and electrophilic groups: —O − , —NH 2 , —NHR, NR 2 , —OH, OR, —NHCOR, —OCOR, alkyls, —C 6 H 5 , vinyls, wherein R is radical selected from the list consisting of alkyl, allyl, benzyl groups, phenyl, substituted phenyl and other aryl (aromatic) groups;
m is number of dopant groups R1 which is equal to 1, 2, 3 or 4,
R2 is a substituent comprising one or more ionic groups from a class of ionic compounds that are used in ionic liquids connected to the aromatic polycyclic conjugated molecule (Core1) directly or via a connecting group,
p is number of ionic groups R2 which is equal to 0, 1, 2, 3 or 4;
wherein the fragment marked NLE containing the Core1 with at least one dopant group R1 has a nonlinear effect of polarization,
wherein a fragment comprising the electro-conductive oligomer (Core2), resistive substituents providing solubility of the organic compound in a solvent and electrically insulating the column-like supramolecules from each other (R4) and/or the ionic groups R3 is selected from structures 98 to 107:

2. The electro-polarizable compound according to claim 1 , wherein the dopant group (R1) is selected from nucleophilic groups (donors) and electrophilic groups (acceptors).

3. The electro-polarizable compound according to claim 2 , wherein the electrophilic groups (acceptors) are selected from —NO 2 , —NH 3 + and —NR 3 + (quaternary nitrogen salts), counterion Cl − or Br − , —CHO (aldehyde), —CRO (keto group), —SO 3 H (sulfonic acids), —SO 3 R (sulfonates), SO 2 NH 2 (sulfonamides), —COOH (carboxylic acid), —COOR (esters, from carboxylic acid side), —COCl (carboxylic acid chlorides), —CONH 2 (amides, from carboxylic acid side), —CF 3 , —CCl 3 , —CN, wherein R is radical selected from the list comprising alkyl (methyl, ethyl, isopropyl, tert-butyl, neopentyl, cyclohexyl etc.), allyl (—CH 2 —CH═CH 2 ), benzyl (—CH 2 C 6 H 5 ) groups, phenyl (+substituted phenyl) and other aryl (aromatic) groups; and
wherein the nucleophilic groups (donors) are selected from —O − (phenoxides, like —ONa or —OK), —NH 2 , —NHR, NR 2 , —OH, OR (ethers), —NHCOR (amides, from amine side), —OCOR (esters, from alcohol side), alkyls, —C 6 H 5 , vinyls, wherein R is radical selected from the list comprising alkyl (methyl, ethyl, isopropyl, tert-butyl, neopentyl, cyclohexyl etc.), allyl (—CH2-CH═CH2), benzyl (—CH2C6H5) groups, phenyl (+substituted phenyl) and other aryl (aromatic) groups.

4. The electro-polarizable compound according to claim 1 , wherein at least one ionic group R2 or R3 is independently selected from the list comprising [NR 4 ] + , [PR 4 ] + as cation and [—CO 2 O] − , [—SO 3 ] − , [—SR 5 ] − , [—PO 3 R] − , [—PR 5 ] − as anion, wherein R is selected from the list comprising H, alkyl, and fluorine.

5. The electro-polarizable compound according to claim 1 , wherein the at least one connecting group is selected from the list comprising the following structures: 29-45, where W is hydrogen (H) or an alkyl group:

6. The electro-polarizable compound according to claim 1 , wherein the at least one connecting group is selected from the group of CH 2 , CF 2 , SiR 2 O, CH 2 CH 2 O, wherein R is selected from the list comprising H, alkyl, and fluorine.

7. The electro-polarizable compound according to claim 1 , wherein the resistive substituent R4 is selected from the group of alkyl, aryl, substituted alkyl, substituted aryl, fluorinated alkyl, chlorinated alkyl, branched and complex alkyl, branched and complex fluorinated alkyl, branched and complex chlorinated alkyl groups, and any combination thereof, and wherein the alkyl group is selected from methyl, ethyl, propyl, n-butyl, iso-butyl and tert-butyl groups, and the aryl group is selected from phenyl, benzyl and naphthyl groups or siloxane, and/or polyethyleneglycol as linear or branched chains.

8. The electro-polarizable compound according to claim 1 , wherein the resistive substituent R4 is C X Q 2X+1 , where X≥1 and Q is hydrogen (H), fluorine (F), or chlorine (Cl).

9. The electro-polarizable compound of claim 1 , wherein the aromatic polycyclic conjugated molecule (Core1) and the dopant groups (R1) form a non-centrosymmetric molecular structure.

10. The electro-polarizable compound of claim 1 , wherein the aromatic polycyclic conjugated molecule (Core1), the dopant groups (R1) and the resistive substituents (R4) form a non-centrosymmetric molecular structure.

11. An electro-polarizable compound of claim 1 , wherein a fragment comprising the aromatic polycyclic conjugated molecule (Core1), dopant groups (R1) and resistive substituents providing solubility of the organic compound in a solvent and electrically insulating the column-like supramolecules from each other (R4) is selected from structures 46 to 97:

Assignees

• Capacitor Sciences Inc
• Capacitor Science Incorporated

Inventors

• Lazarev Pavel Ivan
• Furuta Paul T
• Sharp Barry K
• Li Yan

Classifications

• H10K10/20

  Organic diodes · CPC title

• H10K85/621

  Aromatic anhydride or imide compounds, e.g. perylene tetra-carboxylic dianhydride or perylene tetracarboxylic di-imide · CPC title

• H10K85/6572

  comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole · CPC title

• Y02E10/549

  Organic PV cells · CPC title

• Y02T10/70

  Energy storage systems for electromobility, e.g. batteries · CPC title